4-Hydroxybenzaldehyde → 5-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

HRID 280229ノート

反応式

HRID 280229 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[CH2:21][C:22]1[N:27]2[CH:28]=[N:29][CH:30]=[C:26]2[CH:25]=[CH:24][CH:23]=1.[H-].[Na+].[OH:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1.S(=O)(=O)(O)O>O1CCCC1>[OH:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:21][C:22]2[N:27]3[CH:28]=[N:29][CH:30]=[C:26]3[CH:25]=[CH:24][CH:23]=2)=[CH:36][CH:35]=1

参加物

7

反応物 5

HCID 1264-HydroxybenzaldehydeHCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 233218555-(Chloromethyl)imidazo[1,5-a]pyridine

生成物 1

HCID 540585275-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Imidazo[1,5-a]pyridine-5-methyltriphenylphosphonium chloride (4.29 g), which is prepared from equimolar quantities of triphenylphosphine and 5-chloromethylimidazo[1,5-a]pyridine, is added to slurry of sodium hydride (0.5 g, 50% mineral oil dispersion) in 100 ml of dry tetrahydrofuran at 0° under nitrogen. After 1 hour at 0° a solution of p-hydroxybenzaldehyde (0.61 g) in 15 ml of dry tetrahydrofuran is added. The reaction is allowed to warm to room temperature, is then refluxed for 1 hour, cooled and acidified with dilute sulfuric acid. The aqueous layer is washed with ethyl acetate, adjusted to pH=7 with 50% sodium hydroxide and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated to yield 5-[2-(p-hydroxyphenyl)-ethen-1-yl]-imidazo[1,5-a]pyridine.

後処理

  1. additionis added
  2. temperatureis then refluxed for 1 hour
  3. temperaturecooled
  4. washThe aqueous layer is washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated

出典と根拠

ORDレコード
ord-2a9dd7f796434117aa065e413a387abe
出典データセット
uspto-grants-1986_05
特許番号
US04588732

反応ノート

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